Phenol, pentafluoro-

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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-957.1 ± 2.0kJ/molCcrCox, Gundry, et al., 1969 

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfsolid-1024.5 ± 2.0kJ/molCcrCox, Gundry, et al., 1969ALS
Quantity Value Units Method Reference Comment
Δcsolid-2374.7 ± 2.0kJ/molCcrCox, Gundry, et al., 1969ALS
Quantity Value Units Method Reference Comment
solid,1 bar242.84J/mol*KN/APaukov, Lavrent'eva, et al., 1969crystaline, I phase; DH
solid,1 bar227.1J/mol*KN/AAndon, Counsell, et al., 1968crystaline, I phase; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
260.66298.15Paukov, Lavrent'eva, et al., 1969crystaline, I phase; T = 12 to 329 K.; DH
201.3298.15Andon, Counsell, et al., 1968crystaline, I phase; T = 12 to 377 K.; DH

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Quantity Value Units Method Reference Comment
Tboil416.KN/AFarchan Laboratories, 1990BS
Tboil416.KN/APCR Inc., 1990BS
Tboil416.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Ttriple305.18KN/APaukov, Lavrent'eva, et al., 1969, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple310.62KN/AAndon, Counsell, et al., 1968, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc605.KN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 5. K; TRC
Tc609.KN/AHales and Townsend, 1974Uncertainty assigned by TRC = 6.08 K; TRC
Quantity Value Units Method Reference Comment
Pc38.00barN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 3.00 bar; derived from fit of obs. vapor pressure; TRC
Quantity Value Units Method Reference Comment
ρc2.90mol/lN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.14 mol/l; TRC
ρc2.87mol/lN/AHales and Townsend, 1974Uncertainty assigned by TRC = 0.0287 mol/l; Liquid density determined by magnetically balanced float up to 490 K, see J.L.Hales, 1970-128. Critical D by equation due to Riedel.; TRC
Quantity Value Units Method Reference Comment
Δvap52.2 ± 0.4kJ/molEBSteele, Chirico, et al., 1997, 2Based on data from 323. to 455. K.; AC
Quantity Value Units Method Reference Comment
Δsub67.4 ± 1.6kJ/molVCox, Gundry, et al., 1969ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
44.2393.AStephenson and Malanowski, 1987Based on data from 378. to 428. K. See also Ambrose, 1968.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
378.60 to 428.114.188131377.38-89.447Ambrose, 1968, 2Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
67.4 ± 1.7273. to 299.GSCox, Gundry, et al., 1969See also Cox and Pilcher, 1970.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
12.845305.18Paukov, Lavrent'eva, et al., 1969DH
16.41310.6Andon, Counsell, et al., 1968, 3AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
42.09305.18Paukov, Lavrent'eva, et al., 1969DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
4.04287.Andon, Counsell, et al., 1968, 4CAL
52.83310.6

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.4853248.15crystaline, IIcrystaline, IPaukov, Lavrent'eva, et al., 1969DH
1.134287.crystaline, IIcrystaline, IAndon, Counsell, et al., 1968DH
16.410310.62crystaline, IliquidAndon, Counsell, et al., 1968DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
5.99248.15crystaline, IIcrystaline, IPaukov, Lavrent'eva, et al., 1969DH
3.95287.crystaline, IIcrystaline, IAndon, Counsell, et al., 1968DH
52.82310.62crystaline, IliquidAndon, Counsell, et al., 1968DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
MS - José A. Martinho Simões

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Bromine anion + Phenol, pentafluoro- = (Bromine anion • Phenol, pentafluoro-)

By formula: Br- + C6HF5O = (Br- • C6HF5O)

Quantity Value Units Method Reference Comment
Δr107. ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr66.5 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
66.5423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

C6F5O- + Hydrogen cation = Phenol, pentafluoro-

By formula: C6F5O- + H+ = C6HF5O

Quantity Value Units Method Reference Comment
Δr1372. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase; B
Δr<1630. ± 11.kJ/molAcidBriscese and Riveros, 1975gas phase; HO- + C6F6 -> , acidity probably ca. 320 kcal; B
Quantity Value Units Method Reference Comment
Δr1342. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; B

C20H32O2Zr (solution) + Phenol, pentafluoro- (solution) = C26H31F5O2Zr (solution) + Water (solution)

By formula: C20H32O2Zr (solution) + C6HF5O (solution) = C26H31F5O2Zr (solution) + H2O (solution)

Quantity Value Units Method Reference Comment
Δr-33.5 ± 1.3kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C26H31F5O2Zr (solution) + Phenol, pentafluoro- (solution) = C32H30F10O2Zr (solution) + Water (solution)

By formula: C26H31F5O2Zr (solution) + C6HF5O (solution) = C32H30F10O2Zr (solution) + H2O (solution)

Quantity Value Units Method Reference Comment
Δr-19.2 ± 1.7kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C20H32Zr (solution) + Phenol, pentafluoro- (solution) = C26H31F5OZr (solution) + Hydrogen (g)

By formula: C20H32Zr (solution) + C6HF5O (solution) = C26H31F5OZr (solution) + H2 (g)

Quantity Value Units Method Reference Comment
Δr-143.1 ± 1.3kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C26H31F5OZr (solution) + Phenol, pentafluoro- (solution) = C32H30F10O2Zr (solution) + Hydrogen (g)

By formula: C26H31F5OZr (solution) + C6HF5O (solution) = C32H30F10O2Zr (solution) + H2 (g)

Quantity Value Units Method Reference Comment
Δr-103.3 ± 2.5kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C13H24Zr (solution) + Phenol, pentafluoro- (solution) = C18H21F5OZr (solution) + Methane (g)

By formula: C13H24Zr (solution) + C6HF5O (solution) = C18H21F5OZr (solution) + CH4 (g)

Quantity Value Units Method Reference Comment
Δr-187.9 ± 2.1kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C18H21F5OZr (solution) + Phenol, pentafluoro- (solution) = C23H18F10O2Zr (solution) + Methane (g)

By formula: C18H21F5OZr (solution) + C6HF5O (solution) = C23H18F10O2Zr (solution) + CH4 (g)

Quantity Value Units Method Reference Comment
Δr-174.9 ± 2.9kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C13H24Hf (solution) + Phenol, pentafluoro- (solution) = C18H21F5HfO (solution) + Methane (g)

By formula: C13H24Hf (solution) + C6HF5O (solution) = C18H21F5HfO (solution) + CH4 (g)

Quantity Value Units Method Reference Comment
Δr-178.2 ± 1.3kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C18H21F5HfO (solution) + Phenol, pentafluoro- (solution) = C23H18F10HfO2 (solution) + Methane (g)

By formula: C18H21F5HfO (solution) + C6HF5O (solution) = C23H18F10HfO2 (solution) + CH4 (g)

Quantity Value Units Method Reference Comment
Δr-172.0 ± 1.7kJ/molRSCSchock and Marks, 1988solvent: Toluene; MS

C5H11BrMg (solution) + Phenol, pentafluoro- (solution) = C6BrF5MgO (cr) + Pentane (solution)

By formula: C5H11BrMg (solution) + C6HF5O (solution) = C6BrF5MgO (cr) + C5H12 (solution)

Quantity Value Units Method Reference Comment
Δr-233.9kJ/molRSCHolm, 1983solvent: Diethyl ether; MS

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
9.20 ± 0.02PEMaier and Turner, 1973LLK
9.37 ± 0.02PEMaier, Marthaler, et al., 1980Vertical value; LLK

De-protonation reactions

C6F5O- + Hydrogen cation = Phenol, pentafluoro-

By formula: C6F5O- + H+ = C6HF5O

Quantity Value Units Method Reference Comment
Δr1372. ± 9.2kJ/molG+TSKoppel, Taft, et al., 1994gas phase; B
Δr<1630. ± 11.kJ/molAcidBriscese and Riveros, 1975gas phase; HO- + C6F6 -> , acidity probably ca. 320 kcal; B
Quantity Value Units Method Reference Comment
Δr1342. ± 8.4kJ/molIMREKoppel, Taft, et al., 1994gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291933

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UV/Visible spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source (editor), 1967
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 18956
Instrument SFD-2
Boiling point 143.0

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Cox, Gundry, et al., 1969
Cox, J.D.; Gundry, H.A.; Harrop, D.; Head, A.J., Thermodynamic properties of fluorine compounds. 9. Enthalpies of formation of some compounds containing the pentafluorophenyl group, J. Chem. Thermodyn., 1969, 1, 77-87. [all data]

Paukov, Lavrent'eva, et al., 1969
Paukov, I.E.; Lavrent'eva, M.N.; Anisimov, M.P., Heat capacity, phase transitions, entropy, and enthalpy of pentafluorophenol at low temperatures, Zhur. Fiz. Khim., 1969, 43, 785-787. [all data]

Andon, Counsell, et al., 1968
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F., Thermodynamic properties of fluorine compounds. Part VII. Heat capacity and entropy of pentafluorochelorobenzene and pentafluorophenol, J. Chem. Soc. A, 1968, 2357-2361. [all data]

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Paukov, Lavrent'eva, et al., 1969, 2
Paukov, I.E.; Lavrent'eva, M.N.; Anisimov, M.P., Heat capacity, phase transition, entropy, and enthalpy of pentafluorophenol at low temperatures., Zh. Fiz. Khim., 1969, 43, 785. [all data]

Andon, Counsell, et al., 1968, 2
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F., Thermodynamic properties of fluorine compounds: vii heat capacity and entropy of pentafluorochlorobenzene and pentafluorophenol, J. Chem. Soc. A, 1968, 1968, 2357-61. [all data]

Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturated Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Trimethyl benzene, Pentafluorophenol, 4-tert-Butylcatechol, .alp, J. Chem. Eng. Data, 1997, 42, 1008-20. [all data]

Hales and Townsend, 1974
Hales, J.L.; Townsend, R., Liquid Densities from 293 to 490 K of Eight Fluorinated Aromatic Comp., J. Chem. Thermodyn., 1974, 6, 111-6. [all data]

Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Triethylbenzene, Pentafluorophenol, 4- tert -Butylcatechol, α-Methylstyrene, and N , N '-Bis(2-hydroxyethyl)ethylenediamine, J. Chem. Eng. Data, 1997, 42, 6, 1008-1020, https://doi.org/10.1021/je970102d . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Ambrose, 1968
Ambrose, D., Thermodynamic properties of fluorine compounds. Part V. Vapour pressures of pentafluorobenzene, chloropentafluorobenzene, 2,3,4,5,6-pentafluorotoluene, and pentafluorophenol, J. Chem. Soc., A, 1968, 1381, https://doi.org/10.1039/j19680001381 . [all data]

Ambrose, 1968, 2
Ambrose, D., Thermodynamic Properties of Fluorine Compounds. Part V. Vapour Pressures of Pentafluorobenzene, Chloropentafluorobenzene, 2,3,4,5,6-Pentafluorotoluene, and Pentafluorophenol, J. Chem. Soc. A:, 1968, 1381-1383, https://doi.org/10.1039/j19680001381 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Andon, Counsell, et al., 1968, 3
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F., Thermodynamic properties of fluorine compounds. Part VII. Heat capacity and entropy of pentafluorochlorobenzene and pentafluorophenol, J. Chem. Soc., A, 1968, 2357, https://doi.org/10.1039/j19680002357 . [all data]

Andon, Counsell, et al., 1968, 4
Andon, R.J.L.; Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F., J. Chem. Soc. Sect. A, 1968. [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

Koppel, Taft, et al., 1994
Koppel, I.A.; Taft, R.W.; Anvia, F.; Zhu, S.Z.; Hu, L.Q.; Sung, K.S.; Desmarteau, D.D.; Yagupolskii, L.M., The Gas-Phase Acidities of Very Strong Neutral Bronsted Acids, J. Am. Chem. Soc., 1994, 116, 7, 3047, https://doi.org/10.1021/ja00086a038 . [all data]

Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M., Gas phase nucleophilic reactions of aromatic systems, J. Am. Chem. Soc., 1975, 97, 230. [all data]

Schock and Marks, 1988
Schock, L.E.; Marks, T.J., J. Am. Chem. Soc., 1988, 110, 7701. [all data]

Holm, 1983
Holm, T., Acta Chem. Scand. B, 1983, 37, 797. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]

Maier, Marthaler, et al., 1980
Maier, J.P.; Marthaler, O.; Mohraz, M., Emission spectra of the cations of some fluorosubstituted phenols in the gaseous phase, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 11. [all data]

(editor), 1967
(editor), Koptyug V.A., Atlas of Spectra of Aromatic and Heterocyclic Compounds, 1967, 1, 127. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References